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Synopsis

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Chemistry

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Also known as: 194468-36-5, Javlor (tn), Akos030241699, D09032, J-012596, 4'-deoxy-20',20'-difluoro-5'-nor-vincaleukoblastine ditartrate

Molecular Formula

C₅₃H₆₆F₂N₄O₂₀

Molecular Weight

1117.1 g/mol

InChI Key

YIHUEPHBPPAAHH-GBROPSEISA-N

Vinflunine Ditartrate is the ditartrate salt of vinflunine, a bi-fluorinated derivative of the semisynthetic vinca alkaloid vinorelbine with potential antimitotic and antineoplastic activities. Vinflunine binds to tubulin and inhibits tubulin assembly and disrupts microtubule assembly dynamics. This results in cell cycle arrest in mitosis and an induction of apoptosis.

1 2D Structure

Vinflunine Ditartrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-2,3-dihydroxybutanedioic acid;methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

2.1.2 InChI

InChI=1S/C45H54F2N4O8.2C4H6O6/c1-8-42-14-11-16-51-17-15-43(36(42)51)30-19-31(34(56-5)20-33(30)49(4)37(43)45(55,40(54)58-7)38(42)59-25(2)52)44(39(53)57-6)21-26-18-27(41(3,46)47)23-50(22-26)24-29-28-12-9-10-13-32(28)48-35(29)44;2*5-1(3(7)8)2(6)4(9)10/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t26-,27-,36+,37-,38-,42-,43-,44+,45+;2*1-,2-/m111/s1

2.1.3 InChI Key

YIHUEPHBPPAAHH-GBROPSEISA-N

2.1.4 Canonical SMILES

CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)C6(CC7CC(CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C.C(C(C(=O)O)O)(C(=O)O)O.C(C(C(=O)O)O)(C(=O)O)O

2.1.5 Isomeric SMILES

CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)[C@]6(C[C@H]7C[C@H](CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 194468-36-5

2. Javlor (tn)

3. Akos030241699

4. D09032

5. J-012596

6. 4'-deoxy-20',20'-difluoro-5'-nor-vincaleukoblastine Ditartrate

7. (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-6,7-didehydro-15-[(2r,4r,6s,8s)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2h-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester (2r,3r)-2,3-dihydroxybutanedioate

2.3 Create Date

2010-07-01

3 Chemical and Physical Properties

Molecular Formula	C₅₃H₆₆F₂N₄O₂₀
Molecular Weight	1117.1 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	25
Rotatable Bond Count	16
Exact Mass	1116.42384683 g/mol
Monoisotopic Mass	1116.42384683 g/mol
Topological Polar Surface Area	364 Å²
Heavy Atom Count	79
Formal Charge	0
Complexity	1850
Isotope Atom Count	0
Defined Atom Stereocenter Count	13
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3